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Gilmore is a native of the Texas Panhandle, having been born in Amarillo, Texas, and raised in Lubbock, Texas. His earliest musical influence was Hank Williams and the honkey tonk brand of country music that his father played. In the 1950s, he was exposed to the emerging rock and roll of other Texans such as Roy Orbison and Lubbock native Buddy Holly, as well as to Johnny Cash. He was profoundly influenced in the 1960s by the likes of The Beatles and Bob Dylan and the folk music and blues revival in that decade.

With Joe Ely and Butch Hancock, Gilmore founded The Flatlanders. The group has been performing on and off since 1972. The band's first recording project, from the early 1970s, was barely distributed. It has since been acknowledged, through Rounder's 1991 reissue (More a Legend Than a Band), as a milestone of progressive, alternative country. The three friends continued to reunite for occasional Flatlanders performances, and in May 2002 released a long-awaited follow-up album, Now Again, on New West Records.

After briefly attending Texas Tech University, Gilmore spent much of the 1970s in an ashram in Denver, Colorado, studying metaphysics with teenaged Indian guru Prem Rawat, also known as Maharaji. In the 1980s, he moved to Austin, where his first solo album, Fair and Square, was finally released in 1988.

Gilmore's fans admire his tenor voice, which delivers expressive, pure, country-inflected singing.

In 1994, Gilmore teamed up with Willie Nelson to contribute "Crazy" to the AIDS benefit album Red Hot + Country produced by the Red Hot Organization.

Gilmore appeared as himself in Peter Bogdanovich's 1993 film The Thing Called Love, a love story about young songwriters in Nashville. He also had a small but memorable acting role in the 1998 movie The Big Lebowski as a bowler named Smokey, an aging, emotionally "fragile" pacifist threatened with a pistol by the main character's sidekick (John Goodman). He has also been a guest on The Tonight Show, with host Jay Leno, the Late Show with David Letterman, Garrison Keillor's A Prairie Home Companion on NPR, and the Fresh Air radio program with Terry Gross.

Gilmore's son, Colin Gilmore, is also a singer–songwriter based in Austin, Texas.

Gilmore's song "Braver Newer World" is featured in the 1995 Noah Baumbach film Kicking and Screaming. In 2005 Gilmore released Come on Back, an album of songs his father loved. Gilmore said of the album, "This new album is a compilation of recordings of some old songs that my dad loved. I love them too, and it is a project very dear to me." His version of "Mack the Knife" from the album One Endless Night features on the soundtrack of Jacques Audiard's 2009 film A Prophet (Un Prophète)



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